Performed by the Grateful Dead. Also played by Garcia/Weir/Lesh/Hart 1/17/78 Chicago Acoustic Show with lead vocals by Weir and by Garcia, Bob Weir, Phil Lesh, David Crosby and John Cipollina at a studio session in Novato on August 21, 1971.

Writing credits are often given as Jelly Roll Morton.

"Winin' Boy" is a sexual reference indicating the sexual prowess of the boy/singer. Released versions of the song are usual fairly restrained. Morton however recorded versions of the song for the Library of Congress that were far from restrained.